7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal

Base Information

• Chemical Name: 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal
• CAS No.: 182413-58-7
• Molecular Formula: C₃₉H₄₆O₇
• Molecular Weight: 626.79
• Mol file: 182413-58-7.mol

Synonyms:7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal

Chemical Property of 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal

There total 5 articles about 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal (182413-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / Sn / acetonitrile; H₂O / 16 h / usltasound

2: 97 percent / NaH; n-Bu₄NI / 16 h / 20 °C

3: IDCP / CH₂Cl₂ / 1 h / 20 °C

4: 2.1 g / Zn powder / aq. ethanol / 1 h / Heating

With tin; iodonium(di-γ-collidine) perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; zinc; In ethanol; dichloromethane; water; acetonitrile;

DOI:10.1021/jo001447t

Reference yield:

(S)-1-((2R,3S,4S,5R,6S)-3,4,5-Tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-but-3-en-1-ol (182413-71-4) → 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal (182413-58-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / NaH; n-Bu₄NI / 16 h / 20 °C

2: IDCP / CH₂Cl₂ / 1 h / 20 °C

3: 2.1 g / Zn powder / aq. ethanol / 1 h / Heating

With iodonium(di-γ-collidine) perchlorate; tetra-(n-butyl)ammonium iodide; sodium hydride; zinc; In ethanol; dichloromethane;

DOI:10.1021/jo001447t

Reference yield:

(2R,3S)-3-Benzyloxy-5-iodomethyl-2-((1S,2S,3R)-1,2,3-tris-benzyloxy-4,4-dimethoxy-butyl)-tetrahydro-furan (333717-29-6) → 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-D-gluco-non-8-enose dimethyl acetal (182413-58-7)

Guidance literature:

With zinc; In ethanol; for 1h; Heating;

DOI:10.1021/jo001447t

upstream raw materials:

methanol

methyl 7,8,9-trideoxy-2,3,4,6-tetra-O-benzyl-L-glycero-α-D-gluco-non-8-eno-pyranoside

(2R,3S)-3-Benzyloxy-5-iodomethyl-2-((1S,2S,3R)-1,2,3-tris-benzyloxy-4,4-dimethoxy-butyl)-tetrahydro-furan

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

Downstream raw materials:

(4S,6S,7R,8R)-4,6,7,8-Tetrakis-benzyloxy-9,9-dimethoxy-non-1-en-5-one

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine

(3S,5S,6R,7R)-3,5,6,7-Tetrakis-benzyloxy-8,8-dimethoxy-4-oxo-octanal

(1S,6S,7R,8R,8aR)-1,6,7,8-tetrabenzyloxy-octahydro-indolizine